


The One With Sam's Wedding

by tricia_16



Category: Friends (TV), Supernatural
Genre: A Supernatural Spin on Friends, But with explicit gay sex, F/M, M/M
Language: English
Status: Completed
Published: 2017-11-15
Updated: 2017-11-15
Packaged: 2019-02-03 01:11:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,631
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12737994
Author URL: https://archiveofourown.org/users/tricia_16/pseuds/tricia_16
Summary: The recreation of several Friends episodes using the characters we all know and love from Supernatural!Starring:Castiel as Chandler BingDean Winchester as Monica GellerSam Winchester as Ross GellerGabriel as Joey TribbianiJo Harvelle as Rachel GreenCharlie Bradbury as Pheobe





	The One With Sam's Wedding

**Author's Note:**

> You ever watch a TV show and think, "I can see Cas and Dean as these characters?" This happened to me watching Friends... and now, here we are.
> 
> I called it "The One With Sam's Wedding," because that's the episode title of the episode I'm starting with, but I also kinda love, "The One Where Friends Characters Are a Little Gay."

Castiel has had a very long, albeit happy, day. One of his best friends, Sam Winchester, is getting married tomorrow to Jessica Moore. It’s been a bit of a whirlwind relationship, and he honestly thought Sam would end up married to his on-again, off-again girlfriend, Jo Harvelle and not Jessica, but Castiel has never seen Sam happier. He’s extremely happy for his friend, and very glad to have an excuse to travel to London to be a part of their day.

Tonight was the rehearsal dinner, and the alcohol is really flowing, thanks to the free bar paid for (begrudgingly, by the sounds of the argument currently going on between the Winchesters and the Moores across the room) by Sam’s parents. The alcohol is a good thing though, because right now he’s trying to drown the memory of his apparently _not funny_ best man speech.

Sam’s brother, and Castiel’s friend of several years, Dean, is trying to cheer him up (which is really unnecessary considering the champagne) but kind nonetheless.

“I was totally laughing!” Dean insists.

Castiel clearly remembers a distinct lack of laughter during his entire speech. “Out loud?” he asks, already knowing the answer.

Dean winces. “I didn’t want people to think I was dumb,” he explains.

Castiel knows Dean is struggling with the fact that this is his younger brother’s second wedding, when he hasn’t had the opportunity to get married or even engaged yet. He and Dean have spent a lot of time together, but their friendship isn’t exactly one that’s particularly close or based on a lot of talking about feelings. Even so, he makes sure to check in on him. “May I ask how you’re doing?”

Dean rolls his eyes. “My dad’s riding my ass as usual, but... Sammy’s gettin’ married, you know?” Castiel’s attention is temporarily diverted by what appears to be a very drunk man stumbling towards them. “I’m not gonna let anythin’ ruin that.”

The drunk man claps a hand down on Dean’s shoulder and slurs, “I just want to say that Sam is a very lovely young man.”

Castiel tries to hide his laughter at the amused look on Dean’s face.

Dean answers, “Thanks. He’s alright most of the time,” with laughter in his voice.

The man takes a few steps closer to Dean and then squints at his face, much too close than is socially acceptable. Dean vusibly startles when the man exclaims, “My god!” Castiel chuckles this time, unable to hold it in, and then the drunken man continues, “You must have been a teenager when you had him!”

Castiel’s jaw drops as the man walks away, and he sees Dean stare forwards at nothing with a look of horror on his face. He places a hand on his shoulder and pats it awkwardly, trying to console him in some way.

“That man has obviously imbided in copious amounts of alcohol,” Castiel tells Dean. “He could barely even articulate clearly enough for me to understand what he was saying. There’s _no way_ you look like Sam’s father!”

Dean just glares at him. “Really? Why’d he say that, then? I’m old as shit.”

“Because he’s insane!” Castiel answers quickly. “I’m pretty sure he was the same man who came up to me earlier and congratulated me for my Oscar worthy performance in Titanic.”

Dean laughs dryly before drinking down the rest of his flute of champagne. “Forget it. My dad’s right. I ain’t never gonna get married.”

Castiel shakes his head in disagreement. “I disagree. That is just so... who _wouldn’t_ want to marry you?”

“Yeah, right,” Dean scoffs. “Apparently I look like a single dad with a thirty year old kid,” he says bitterly.

“Now you’re just being ridiculous,” Castiel chastises him. “It looks like we both need more champagne though, so come on.”

Dean follows along, and as the night continues, they both drink far more than their share of bubbles. Castiel can hardly tear his eyes away from how gorgeous Dean is with his eyes shining with laughter and his cheeks flushed from alcohol. His freckles are barely visible through the blush, but Castiel knows they’re there. Eventually, they make their way up to Dean’s hotel room and he makes sure Dean gets inside safely before he makes the trip down the hall to his own room.

He uses the bathroom and changes into his favorite bee printed set of pajamas for bed. He takes out his Kindle and climbs under the cover, ready to read until he gets tired like he does every night. His head’s still spinning slightly, but he’s able to concentrate on the words, and he doesn’t know how long he’s been reading when there’s a knock on the door.

He gets up and looks through the peep hole, surprised to see Dean standing there. He opens the door to let him in and says, “Hello, Dean.”

Dean eyes his pajamas and grins. “Nice jammies. You’re really livin’ it up in London, huh?”

Castiel flushes. “My apologies. I wasn’t exactly expecting company after -“ he glances around and sees the clock radio on his bedside table “... 9:15,” he finishes lamely.

“Is Gabe here?” Dean asks, looking around him at the extra bed in the room.

“No. We passed each other in the hallway when I was on my way back to my room earlier. He was with one of the bridesmaids and had a bottle of champagne under his arm,” he says, knowing that’s enough of an explanation for Dean. He sees a wave of disappointment cross over Dean’s features and his heart goes out to him. “Forgive me for overstepping if I am, but you’re not still upset about what that drunk man said earlier, are you?”

Dean snorts. “Wouldn’t you be?”

“I understand why you might feel uneasy,” Castiel answers honestly. “It’s been an emotional couple of days. Your dad’s been unkind to you, and you’ve had a lot to drink, but you really should try to ignore what that man said. You were honestly the most gorgeous man in the room tonight.”

Dean’s eyes catch his and a small smile comes to his lips. “You think?”

He sounds surprised, Castiel notices wryly. Surely he must know he’s unbelievably attractive by now. “Of course,” Castiel says. “You’re the most gorgeous man in most rooms,” he adds.

Then, before he can even begin to react, Dean has his arms wrapped around his waist and he pulls him in with one hand pressed against his back to capture his lips in a searing (if somewhat messy) kiss. It takes Castiel a second to process what’s going on, but then his lips move against Dean’s easily, and he opens his mouth to accept Dean’s tongue that’s prodding against his lips. Dean lets out a low moan and Castiel comes back to himself.

He wrenches their lips apart and takes several steps back, putting some much needed distance between them. “I’m sorry. I’m so confused. You and I just... made out.” It sounds bizarre even as he says it. “You and I are making out?”

Dean looks nervous now that Castiel has stopped kissing him. “Not anymore, apparently,” he answers with a sigh.

“But... we don’t do that. We’ve never -“

Dean shrugs. “I know. I just thought it might be fun for a night, you know.”

Castiel narrows his eyes at Dean. “How drunk are you?”

Dean smirks as he takes a step towards him. Castiel tries to pretend his heart isn’t hammering in his chest and his dick isn’t still swelling between his legs.

“Drunk enough that I know I want you.” Castiel’s lips part and he realizes he’s breathing heavily. “Not so drunk that you should feel bad about takin’ advantage of me.” He bounces his eyebrows at the last part and Castiel chuckles in spite of himself.

Dean certainly seems to be aware enough of what’s going on. And it’s not as if he has the willpower to resist a man who looks like Dean Winchester in the first place. “That sounds like an acceptable amount,” he says, his voice rough.

Dean grins at him before lying a hand on his chest and beginning to push Castiel back towards the bed as their lips crash together again. Dean’s a fantastic kisser. He’s a little over eager, and a little messy (likely due to the alcohol), but Castiel’s body reacts to him in a way he doesn’t remember ever experiencing before. Dean tastes like the champagne they were both drinking, and he can still smell the musk of his shaving cream or aftershave on his face. His lips are full and plush, and Castiel can’t help the whine that slips out of him when Dean sucks his bottom lip between them.

Dean breaks the kiss and puts his champagne glass down on the end table. “Know what’s kinda weird?”

Castiel deflates, thinking their moment is over and he’s going to have to finish himself off before he goes to bed. There’s no way this hard-on is going away on its own. “What?”

Dean gestures between them and climbs onto the bed. Castiel follows him until they’re laying side by side. “This doesn’t feel weird.”

Castiel smiles genuinely. “I agree.”

Dean leans over and kisses him again, pressing their lips together passionately and trailing his hand down his chest. “You’re a really good kisser,” he admits, and Castiel registers how he sounds slightly surprised.

“Well, I _have_ kissed four men,” Castiel explains. Dean snorts, and Castiel shuts him up by pulling him back down by the back of his neck to kiss him some more. He can feel Dean’s erection pressing against his leg and breaks their kiss to ask nervously, “Would you like to get more comfortable?”

Dean nods eagerly, and he gets up to pull the blankets off of the bed. Castiel takes the opportunity to get to his feet again and rid himself of his pajamas. As much as he loves the bees, he’s assuming that Dean won’t be aroused by them, and he _really_ wants him aroused right now. Dean looks up and does a double take when he sees Castiel fully naked on the other side of the bed.

“Dude, that was _quick_!” Dean exclaims.

Castiel flushes again and says quietly, “It bodes well for me that speed impresses you.”

Dean snorts again and starts unbuttoning his dress shirt before he pauses. “We’re gonna see each other naked,” Dean warns him.

Seeing as Castiel is already fully naked, he’s not too worried about that. “Yes,” he answers eagerly, watching as Dean keeps going and his muscular stomach is revealed inch by tantalizing inch. Dean unbuttons the tiny buttons at his wrists, and then shrugs his shirt over his shoulders and lets it fall to the floor. Castiel is surprised his tongue isn’t unrolling across the floor like a cartoon.

Dean’s body is unbelievable. His skin is tanned, his arms are thick with muscle, his shoulders are broad, and his stomach is (mostly) flat. Castiel would never say it aloud, but he thinks the little bit of pudge around Dean’s middle is endearing. Now he knows where all that pie goes. 

Dean’s fingers find his belt and work the buckle. He makes eye contact with Castiel again, and then he pops the button, drags down his zipper, and wiggles out of his pants and boxers.

Castiel eyes his erection standing almost straight out, and can feel his mouth begin to water. He clears his throat and tries to force himself to look back up at Dean’s face. “I think it’s fairly safe to assume that our friendship is effectively ruined,” he says seriously.

Dean laughs and crawls back onto the bed. Castiel meets him in the middle, and Dean wraps his hand around his waist, tugging him until he’s settled into the vee between his legs. “We weren’t that close anyway,” he grins, and then they’re kissing again, and it’s _glorious._

Dean presses his hips down until their hard cocks are slotted together, and they both let out a breathy sound of pleasure when Castiel registers the _beep-beep_ of a key card being granted access to his room.

Dean must hear it too, because he pulls away and his eyes go wide. Next thing Castiel knows, Dean is diving under the covers and Gabriel is strolling into his room.

“Oh! G-gabriel Gabe! Hi!” Castiel says, cringing inwardly at just how _off_ he sounds.

“Hey, Cassie,” Gabriel beams, strolling over to his side of the room.

“Hi Gabe!” Castiel says, before he realizes he already said that. He has an overwhelming need to fill the silence. “I was just watching a documentary...” he lies, suddenly realizing the television is turned off and trying not to draw attention to the fact.

Gabriel flicks his eyes between the TV and and Castiel in bed with his pajamas on the floor in a heap, and his eyes go wide while a grin spreads across his face. “Oh, man! I am _so sorry_ ,” he laughs.

Castiel’s face flushes. “No! No, no, no!”

Gabriel snorts. “Hey, no judgement from me if you wanna beat the meat. I’ll stop being such a cockblock in just a minute. I’m still making magic happen with my bridesmaid,” he grins. “Where’s those condoms you brought?”

“In my bag. There,” Castiel gestures to it on the other side of the room.

“Ah ha!” Gabriel says triumphantly.

That’s when Castiel realizes he could probably use a condom.

He clears his throat before he says awkwardly, “Um. Can you please leave one of those behind? And a packet of lube?”

Gabriel swivels to give him a look of confusion. “...for just you?”

Castiel shrugs. “That’s right.”

Gabriel’s expression changes from confusion to pity. “Look, why don’t you get some clothes on and come downstairs with me. There’s lots of hot guys down there, and I’m already set with my bridesmaid, so they’re all yours! I can be your wingman!”

“Um, no. No, thank you. I’m... perfectly content staying here. Alone,” he adds. Gabriel is really going to think he’s a freak after this.

Like he thought, Gabriel gives him a funny look but shrugs. He takes a few steps closer and tosses a condom and a packet of lube onto his bed. “Here ya go, buddy. Go nuts,” he adds, and gives him an exaggerated wink before he leaves again.

Dean comes up from under the covers again and though he’s slightly flushed, he’s grinning like he thinks everything that just happened is hilarious. If he wasn’t so unbelievably sexy, Castiel might kick him out of bed just to spite him. Instead, he closes the distance between them and crushes their lips together. This kiss is just as good as the last few have been, but there’s a heightened sense of urgency since they’re naked together in a bed and they were already interrupted once.

This time it’s Castiel who rolls Dean over onto his back and positions himself between Dean’s legs. Dean lifts his hips and their cocks brush together, and Castiel’s is quickly coming back to life after waning with Gabriel’s presence.

He can’t keep kissing Dean when he can feel the hard line of his erection pressing against his own, too overwhelmed with pleasure, so he drags his lips down the side of his face and nibbles his way across his strong jaw.

“You still wanna do this?” Dean asks him.

“God yes,” Castiel answers quickly. He nips his way up to behind Dean’s ear, and runs his tongue along the shell of his ear. “Do you?” he whispers, taking Dean’s earlobe between his teeth and giving a gentle tug.

Dean’s breath hitches and he says, “Want you in me.”

Castiel exhales on a groan, giving into his desire and biting down on Dean’s exposed throat. Dean’s hands grip at Castiel’s back, his blunt fingernails digging into his skin, and Castiel lets his hips thrust down towards Dean. Dean hisses before his hips shoot back up, and they settle into a rhythm of moving together and thrusting against one another while Castiel takes his time exploring Dean’s neck, throat, collarbone, and chest with his lips and hands.

“Want you, Cas,” Dean breathes, rolling his hips again to emphasize his point. “Get your fingers in me.”

Castiel closes his eyes briefly and tries to grasp for control. He hasn’t been with anybody in years, and he’s extremely attracted to Dean. He needs to get a grip before this is over much sooner than either of them want it to be.

He turns away from Dean to search for the lube, and grabs it once he locates it. He tears the packet open with his teeth and squeezes a small amount onto his fingers. He wants to make sure he has enough for the main event, and there’s no way he’s getting out of bed if he can avoid it.

Dean already has his head thrown back, his eyes squeezed closed, and his hands fisted in the sheets beneath him like he can’t possibly wait another second for this. He spreads his legs wider, and Castiel can _see_ how badly he wants to be filled all over his face. It’s unbelievably arousing.

“You are - so, so sexy,” he praises him, knowing the words aren’t enough to describe how absolutely gorgeous he looks right now.

Dean whimpers. “Please, Cas.”

How could Castiel possibly deny him anything? He cups Dean’s balls in his hand, rubbing them gently and earning a moan from Dean, before he moves them to the side and slides a single digit along his crack.

“Oh fuck,” Dean whispers.

Castiel has never been with a man who seems to want this as bad as Dean does right now. He circles his rim with a finger, slowly, watching every flicker of desire on Dean’s face before he slowly slides one finger into his opening. He’s tight and hot, and Castiel moans along with Dean while he starts fingering him open. Before today, he’s always considered prep a boring but necessary part of sex. But now? Now he’s in heaven. Watching Dean come undone beneath him with each thrust of his fingers inside of him is the most erotic thing he’s ever seen. Dean lets out needy whines, sighs of pleasure, and takes sharp breaths with every pass of his fingers. By the time he has two inside of him, scissoring him open, and feeling around for his prostate, he himself is so hard it’s actually bordering on painful.

The first time he brushes against Dean’s prostate, Dean arches his back and lets out the most delicious sound Castiel has ever heard. “Holy shit,” Castiel groans in response.

“There, Cas,” Dean tells him needlessly.

“I got that, believe it or not,” Castiel replies, prodding it again and watching Dean’s hips come off the bed again.

“ _Oh fuck_ , feels so good,” Dean groans. “More. I’m ready for another one.”

More lube and a third finger stretching Dean open is just as arousing as two fingers was. He can’t resist the sight of Dean’s cock lying heavily on his stomach any longer, and finally leans over to take it into his hand.

“Ahhh! _D-don’t!_ ” Dean chokes out, eyes wide. “I’m too close. Way too close.”

Castiel has to swallow down his own desire. He’s never seen anybody so turned on because of his fingers before, and it’s having a rippling effect on him as well. “I have never - wanted - anything - like _this_ ,” Castiel pants, watching him.

“Take me,” Dean says quickly. “I’m ready. I’m so fucking ready.”

Castiel pulls his fingers out, and passes Dean the condom packet to open. Dean rips it open, and Castiel gets onto his knees so he can roll it onto him. His jaw unhinges and his eyes roll back in his head when he feels Dean’s hand on him, and he’s only brought back to earth when Dean says, “More lube?”

His eyes fly back open and he squeezes the remainder of the packet onto his cock, unable to hold in the soft groan that slips out of him when he slicks himself up. “Cas, come on,” Dean urges him.

He pulls his hand away, wipes the excess lube off of his hand onto the blankets, and positions himself between Dean’s legs again. He lines himself up at his entrance, and Dean pulls him down into another kiss before Castiel can push inside. Dean’s kiss is desperate and needy, and Castiel can _feel_ how much he wants this sparking between them. Dean proves his point when he wiggles his ass underneath him, and Castiel lets out a small huff of a laugh against his lips before he breaks away to look down between their bodies.

He reaches down to hold himself in place, and watches as he shoves his hips forwards and plunges inside of his friend. Dean is incredibly tight, even after the prep, but he opens for him perfectly. Castiel watches his dick disappear into Dean’s ass inch by inch, and sheathes himself completely within the encompassing warmth of Dean in seconds.

“Holy shit,” Dean groans.

Castiel lowers his head to Dean’s, gasping for breath, trying to think of anything except for how fucking good Dean feels squeezing around him. Dean lifts his lips to Castiel’s, kissing him again, and Castiel takes the distraction happily. Dean licks into his mouth filthily, and Castiel chases his lips as his head falls back onto the pillow. Dean tilts his head slightly, letting him dive in deeper, and he elicits another sound of contentment from Dean’s throat. His testicles are pressed tight to Dean and each tiny movement of their bodies jostles them and shoots additional pleasure through him. Dean’s hands on his back slide down to his ass, and he feels him give his asscheeks a quick squeeze before he pulls him towards him.

Castiel gets the message.

He breaks their kiss in favor of looking into Dean’s eyes, watching for any sign of pain or discomfort, when he slides out a few inches and pushes back inside slowly. Dean’s eyes are heavily lidded, and there’s nothing but pleasure within them.

“I’m good,” he says quickly. “Just fuck me. I need this so fucking bad.”

Castiel nods and pulls almost all the way back out before he slides in again. Dean’s mouth drops open and his head tilts back again. “Oh god, _yes_ ,” Dean encourages him. Castiel pulls out to push in again and again, fucking him in long but steady strides. Dean’s hands never leave his ass, and he pulls him forwards with each thrust. He loses track of time with the slick slide of their bodies coming together again and again.

Castiel is getting close to his orgasm and isn’t nearly ready to be finished with Dean yet, so he pulls out and flips Dean over so he’s on his stomach to switch positions. Dean lets out a sound of surprise, but Castiel is already grabbing him around the waist and hefting him up until he’s on his hands and knees. Dean does one better and gets up so he’s standing on his knees and bracing his hands on the headboard in front of him. Castiel is momentarily struck stupid by the view of Dean’s muscular back and unfairly _perfect_ ass displayed for him. “C’mon, Cas. Keep fucking me. _Hard_ this time,” he asks.

“I can’t,” Castiel admits. Dean shoots him a concerned look over his shoulder and Castiel continues, “It’s been too long. You feel too good.”

Dean shakes his head. “Don’t care. Want you hard and fast. I’ll get there,” he promises. He wiggles his ass again, sticking it out and tempting Castiel.

It’s with a throaty growl that Castiel grips him by the hips and lines himself up again before thrusting into him hard from behind. He buries himself in one sharp thrust, and Dean lowers his head to the headboard in front of him with a curse.

“Yes, _yes_ , exactly like that, _fuck_ ,” Dean encourages him. Castiel pulls out again and slams into him, and Dean calls out. “God, yes, there Cas. Again!”

“ _Dean,”_ Castiel groans, snapping his hips forward over and over, lowering his mouth to the curve of his shoulder and leaving open mouthed kisses along his perfectly tanned skin.

Dean starts pushing back against him, almost bouncing on his cock, working himself exactly the way he wants to, meeting each of Castiel’s thrusts halfway and driving him closer and closer to the edge. Castiel can’t take his eyes off of the curve of Dean’s lower back and the way the muscles flex with every roll of his hips. He could come just from watching his back, he’s absolutely sure of it.

“Touch me,” Dean begs him. Castiel reaches around him and wraps his hand around Dean’s rock hard cock. “Jesus Christ,” he says on an exhale.

Castiel barely has to move his hand at all. Dean’s alternating seamlessly between rolling his ass down onto Castiel’s cock and thrusting forwards up into his hand. He’s obviously wringing every ounce of pleasure from Castiel he can and Castiel wants nothing more than to give everything he can to him. He twists his wrist, circling his cockhead, and Dean calls out.

“Ah! Cas! I’m - _oh fuck_ -“ he gasps, and then Castiel can feel it as Dean’s entire body tenses. He smirks and runs his thumb across the slit of his cock, and then it pulses in his hand before Dean comes with a shout. “ _Castiel_!” Dean’s body shakes while Castiel strokes him through his orgasm, and once he’s spent, he slumps forwards and braces his upper body on the headboard.

Finally, Castiel lets go and fucks into Dean as hard and fast as he can, chasing his orgasm instead of denying it, and it’s only a minute later that he buries himself deep, deep inside of Dean, grips Dean’s hips desperately and comes _hard_ inside of him. Unbelievable pleasure courses through his body as he lazily thrusts through his orgasm. He lets his forehead fall between Dean’s shoulder blades as he tries to catch his breath.  

“Holy shit,” Dean says, breaking the silence.

“Yeah,” Castiel agrees, laughing a little. He pulls out of Dean carefully and pulls off and ties the condom. “I’ll go get you a cloth,” he offers.

A little while later, they’re both cleaned up, and lying in Castiel’s bed in two carefully spaced out boneless heaps. Castiel hates the space between them but he doesn’t know if it’s appropriate to snuggle given the circumstances.

“Should I take off?” Dean offers.

“I don’t mind if you stay,” Castiel says carefully.

“I’m uh, kind of a post-sex cuddler if I can get it,” Dean admits.

Castiel breathes a sigh of relief, and pulls Dean in against him so that his head rests on his shoulder. That’s _much_ better.

Castiel has just about dropped off into sleep when Dean says, “This is so fucked.”

Castiel huffs out a soft laugh, completely agreeing with the sentiment. There’s no way their group of friends isn’t going to notice that something’s changed between them. “Let’s not worry about that for tonight. I’m tired,” he says gently.

Dean lets out what sounds like a happy sigh. “Kay. G’night, Cas.”

Castiel smiles to himself happily, knowing Dean can’t see him. “Goodnight, Dean.”

 

* * *

 

The very next thing he’s aware of, Sam is in his room, shouting excitedly, “I'm getting married today! Yessss!”

Castiel barely has a second to gasp his surprise before Sam is gone again, the hotel door clicking shut behind him.

Dean pops up from beneath the covers and says with wide eyes, “Do you think he knew I was here?”

Castiel rolls onto his back and scooches up so he’s in a sitting position. He feels weird with his upper body on display, so he pulls the blanket up to his armpits. Dean does the same. He suddenly feels incredibly awkward, and hyper aware that he’s in bed, _naked_ , with his friend Dean.

He swallows down some of the awkwardness and tries to say as normally as he can, “Well... we’ve never done _that_ together before last night.”

Dean laughs, but Castiel can tell it isn’t genuine. “Nope,” he replies, popping the _p_.

He doesn’t say anything. Castiel thinks about what he should say. After several seconds of more awkward silence, he says, “So, um... how are you? Are you... okay?”

Dean flushes. “Oh. Yeah. Yep. Fine,” he answers quickly. “You?”

“Me?” Castiel responds. “I’m good. You?” Dean finally meets his eyes and Castiel realizes he already asked him that. “We, um, already covered you, huh?” he says with a crooked smile.

Dean grins back at him. “We did. I, uh, better get going.”

Castiel bobs his head. “Yeah, absolutely.”

Dean goes to get out of bed but then shoots him a shy smile. “Could you, maybe, not look?”

Castiel’s eyes go wide and he turns his head completely away from him. “Of course. I don’t even _want_ to look,” he lies.

A few minutes later, Dean says, “We’re not gonna tell anybody about this, are we?” he asks.

Dean basically answered that question with his question, so Castiel agrees. “No.”

Dean nods. “Okay. So I’ll see you later, then. At the wedding, I mean.”

Castiel figures it’s safe to look now, so he turns towards him and nods. “See you later.”

Then Dean walks out of his room and Castiel slumps sideways onto the bed.

_What did they do!?_

 

* * *

 

Gabriel strolls into his hotel room the next morning to the phone ringing and Castiel nowhere to be found.

”Hello?” he says, answeing the phone.

” _Now_  he answers the phone!” Charlie says on the other end. “Where the hell have you been?”

”Hey Charles!” Gabriel exclaims. “I spent the night with this incredibly flexible...”

”I don’t wanna hear about her!” Charlie interrupts.

Gabriel grins. “I know you’re jelly, but you’re still my favorite girl,” he promises.

“Gabriel! Get your tiny head out of your ass and listen to me! We have a code red emergency situation devolving in real time! Jo is coming to London! She’s on her way right now!”

Gabriel’s smile spreads genuinely. “That’s great!”

“No!” Charlie shrieks. “It’s _not_  great, you dummy! She’s coming to tell Sam that she loves him!”

Gabriel frowns. “But Sam loves Jess.”

”I know that!” Charlie growls. “You have to stop her! She’s going to ruin the wedding!”

Gabriel nods. “Got it. I’m all over it, okay? Don’t even spare it another thought. The Trickster’s got this.”

”Okay,” Charlie relents. Her voice is pitched low and dripping with suggestion when she says, “So just how flexible was this girl you were about to tell me about?”

Gabriel bounces his eyebrows and launches into the tale.

* * *

 

 

A little while later, Castiel comes out of the bathroom after a much needed shower (where he absolutely did not think about Dean...) wearing a bathrobe, and sees Gabriel on his bed.

“Hello,” Castiel greets him.

“Have you seen Dean?”

Castiel’s back goes up immediately and he responds, “Dean and I are not _seeing_ each other.”

Gabriel gives him a look of confusion before his face breaks out on a grin. “What?” he laughs.

Castiel realizes what he just said and hears himself echoing Gabriel’s question, “... what?”

Gabriel shakes his head. “Stop being weird, Cassie. We’ve gotta find her. Charlie just called and she said Jo’s coming to tell Sam that she still loves him!”

Castiel’s jaw drops and his eyes go wide with shock. “Oh no!” he exclaims.

“I know, right? Not my preferred threesome, if you know what I mean,” he jokes, and Castiel just looks blankly at him. “Anyway. That’s why we need to find Dean! Do you know where he is?”

Gabriel mentioning Dean _again_ makes him feel like their secret is about to be exposed and he overreacts. “For the last time, I haven’t seen Dean, and I would appreciate it if you would stop asking me insistantly about him! You might as well shine a light in my eyes and put me in a room with one way glass!”

Gabriel is looking at him like he has three heads, and without knowing what else to do, he grabs his duffel bag and storms back into the bathroom to get dressed.

He drags a hand through his hair, already messing it up, and sighs heavily. He is _not_ cut out for this.

 

* * *

 

Sam stands in front of Castiel in the church, stoically repeating, "I do.  _I_ do. I  _do_ ," putting different emphasis on each word each time he repeats them.

Castiel nods seriously. "Yes, I believe you're right. You should definitely go with the second one."

Sam is obviously incredibly nervous, "Really?" he asks desperately.

Castiel nods, gives him a pat on the shoulder to reassure him, and says, "You're going to do great, I promise."

He cranes his neck to get another look around the church and is satisfied when he doesn’t see Jo anywhere yet. Gabriel is keeping an eye out in the hallway, but there are several entrances and who knows which way she’s going to come in.

 

* * *

 

Jo Harvelle strolls through the hallway leading to the chapel, and doesn't even give the sight of Gabriel pressed up against the wall by a young woman in a fancy dress a second glance. She would've been more surprised if he wasn't hooking up with one of the bridesmaids, really. Her only focus is on finding Sam and telling him that she loves him,  _has_ loved him for as long as she can remember, and can't stand the thought of him getting married without him knowing the truth about her feelings.

She throws open the door, and the first thing she sees is Sam kissing Jessica, both of them in their full wedding outfits, looking as happy as they should on their wedding day.  
  
She's frozen in place. She can't ruin this day for him, can she? If she  _really_ loves him, and god, does she, she should just let him be happy. She's so lost in her own thoughts that she doesn't realize Jessica has walked away until she hears Sam call her name. "Jo?"

She turns her head towards him and her heart tumbles in her chest when she sees the excited smile on his face. This smile was worth the flight and fighting with the damn flight attendant all on its own.  

"Holy crap, Jo!" he exclaims. He crosses the room towards her and pulls her in for a tight hug. She fits into his arms perfectly, the way she always has, and she lets herself take in the familiar scent of him while she wills away the tears that are springing to her eyes. "What happened? Why made you decide to come?"

She looks up at him, his hair falling in his face, as happy as she's ever seen him, and she replies, "I just came..." she rests her hand on his chest near his heart out of habit, and then pulls her hand away when she realizes she probably shouldn't do that anymore. He's not hers anymore. "I just needed to tell you..." she takes a deep breath and looks into those kind, green eyes, and finishes, "Congratulations, Sam."

He hugs her again, and she can barely hold back her tears. Years of dating, kissing, making love, and laughter run through her head in a blink of an eye.  _Goodbye, Sam_ , she thinks to herself sadly.

 

* * *

 

The wedding is starting, and Castiel crosses the room to escort Dean down the aisle. Two weeks ago when they first discussed this, they both thought it was hilarious that the two of them would walk down the aisle together. Now, Castiel's legs are shaking with nerves and he's positive he's going to trip and fall before he reaches Dean.

He doesn't, though. Dean hooks his arm through Castiel's, and Castiel says quietly, "What we did last night was..."

"Stupid," Dean finishes for him just as quietly.

"Absolutely, insanely stupid," he agrees. Somebody seated in the pews smiles at him, and he nods his head in response, pasting a fake smile onto his face. He can feel Dean's touch practically burning through his suit jacket. All he can think about being this close to Dean is how he felt clenching around him. How he looked when he was fucking himself back onto his cock...

"What the hell were we thinkin', huh?" Dean asks, but it doesn't sound convincing. In fact, he squeezes Castiel's bicep a little, and when Castiel glances down at him, Dean winks at him.

Castiel feels his breath hitch, and Dean smirks at him. Castiel takes a chance, a really big, _gigantic_ chance, and says, "I can come by your room later tonight, if you want?"

Dean squeezes his bicep again and his eyes are glittering with mischief when he answers, "Abso-fuckin'-lutely."

 

* * *

 

Jo can hardly look at Sam and Jess up at the altar. They look gorgeous together, and they're both radiating happiness... and it's breaking her heart, one second at a time.

Her eyes are glued to them like a train wreck. She knows she's going to regret this, but she looks directly at Sam when she hears the minister say, "Friends. Family. We are gathered to celebrate here today the joyous union of Samuel and Jessica. May the happiness we share with them today be with them always. Now, Jessica, repeat after me. I, Jessica..."

Jessica's smile is blinding when she repeats, part by part, “I, Jessica, take thee, Sam, as my lawfully wedded husband. In sickness and in health, until death parts us."

Then it's Sam's turn. His voice is clear and serious when he begins, "I, Sam, take thee, Jo..."

And that's when Jo's heart drops into her stomach.

Sam seems to realize what he said with horror when Jessica flinches, and quickly stammers, “ _Jessica_. I meant Jessica, obviously. Of course I meant Jessica. J names, you know,” he laughs nervously.

The minister looks at Jessica and says, “Shall I go on?”

Jo’s perched on the edge of her seat, waiting with her breath held for Sam’s response.

Jessica pastes an obviously fake smile on her face, but nods. “Y-yes. Yes,” she says more clearly. “Please, keep going.”

The minister smiles. “I think we should probably start again. Sam, please repeat after me: I, Sam, take thee, _Jessica_...”

Sam clenches his jaw at the minister but says, “I, Sam, take thee, _Jessica_...” he laughs nervously. “Like there’d be anybody else,” he says, trying to make a joke that falls flat and makes Jo’s stomach twist uncomfortably. “As my lawfully wedded wife. In sickness and in health, until death parts us.” He takes a short breath and then adds, “Really. It’s true. I do. _Jessica_ ,” he adds again.

Jo thinks Jess looks like she’s about to puke. Or deck Sam. Jo’s pretty close herself and she doesn’t even _like_ Jess. They exchange rings, with Jess all but shoving Sam’s ring onto his finger violently, which Sam tries to laugh off. And then the minister says, “It is my pleasure to announce them husband and wife. You may now kiss the bride.”

Sam leans in to kiss Jessica, but Jessica backs away, and after several super awkward attempts at Sam trying to kiss Jess and Jess blocking his every move, he finally kisses her on the cheek, and and Jess storms down the aisle and out of the church on her own with Sam chasing behind her. 

Jo barely hears John Winchester comment behind her in a whisper that still somehow carries, “This is even worse than when he married a lesbian.”

Jo covers her mouth to hide her laughter, and instantly feels like the worst friend in the world.

**Author's Note:**

> So my plan is to redo an episode per chapter, until I’m done and/or tired of doing this lol Each chapter can be read on it’s own just as you can watch an episode of Friends on its own, but they will of course relate to one another.
> 
> Remember, comments are love! Let me know what you think of this!


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